Sugar Daddy

My name is Roger and I have been happily married to my wife, Maryanne, for over thirty years. I deeply love my wife and have to say that marrying her was the best thing I ever did in my life. Like most men when they were younger, I partied hard, slept with my fair share of ladies but I settled down when I met my future wife less than a year after I graduated college. We have two wonderful children, Kenny who is a very successful software programmer out in California, and Jenny who is now 20 years old and going into her junior year in a college several hundred miles away from home.

This story goes back to when Jenny was an eighteen-year-old senior in high school. At the time, Maryanne was in the full throws of menopause that produced the typical hot flashes and mood swings that come along with the change of life. It was challenging dealing with the hormonal swings at times. I swear, she would get pissed off at me for simply breathing or being in the same room with her but she was also my long-time, loving wife and I felt a duty to help her manage getting older. I was getting older too. My hair was starting to turn gray and I was developing a small beer belly but still managed to stay in decent shape by going to the gym or using the treadmill at home.

Maryanne had also begun to lose interest in having sex for several years by then. It happened so gradually, it's difficult to say when it exactly ended. She felt she wasn't sexy anymore after gaining several pounds, suffering hormonal changes and changes in her body such as sagging breasts and getting a couple of wrinkles. As much as I tried to convince her she was still sexy, she lost the desire to have sex. That left me to jerk off when I was alone or out of town on business.

My wife even hinted several times that she wouldn't blame me if I found some satisfaction on the side. I never seriously considered it because I loved my wife too much to ever cheat on her. Besides, between working sixty hours per week, dealing with a teenage daughter with her own mood swings, and a menopausal wife, trying to balance a girlfriend didn't seem like a feasible option.

Things went further south after my wife lost her tolerance for my snoring, I moved out of our bedroom into my son's now-vacant room which afforded me more of an opportunity to masturbate also. It's not like the move was going to harm our sex life and it reduced the tension between my wife and me by allowing her to get a better night's sleep. I also didn't have to put up with her waking me up with an elbow to my ribs for snoring too loudly, so I slept better too. I was resigned to the fact that sex was going to be something that happened on rare occasions and mostly because my wife felt obligated to at least try to retain some semblance of a sex life.

I'm a very successful businessman, working for a large insurance company and we have a four-bedroom suburban home with a large backyard and inground pool. My income allowed us to take luxurious vacations to Europe or the Caribbean so life wasn't all bad. We had the ideal life except for our lack of a sex life. I figured it was a small price to pay for what was otherwise a life others dreamed of having.

As our sex life waned, I began to work longer hours, figuring I'd try and put money away for possible early retirement. I took advantage of my Executive Vice-President title and seniority to grab a few out-of-town accounts to help pad my retirement savings. Sometimes Maryanne would come with me on my out-of-town trips but she had her own career at a local bank to consider and my business trips could be boring for her, especially if I was dining with clients.

Our daughter, Jenny, was in her senior year of high school, had her own car, and had a lot of freedom now that she was eighteen. There were some battles between my wife and daughter on how much freedom she had or wanted but I tried to stay out of those fights the best I could. Jenny was a good kid with a big heart and wasn't doing half the things I was doing when I was her age so I rarely hassled her. I hardly noticed what was going in our household anyway.

On the rare occasions when I would make it home in time for dinner or when I came back from a business trip, I did notice that one of Jenny's friends, Sara, was spending more time at our house. I didn't mind that she would be at our dinner table or spending the night on weekends, after all, that's what friends do. Sara was a nice polite young lady so it wasn't a problem at all. As it got into the spring of Jenny's school year, I noticed Sara was at our house more often than not. I found it strange but it didn't bother me although I was curious as to why.

When I asked Maryanne about all of the time Sara was spending at our house, she told me that Sara's step-father was a jerk and there was a lot of tension between them so she liked being around our house. I got the impression that her step-father didn't want her around because she wasn't his child so she made herself scarce whenever she could. Sara's parents didn't seem to mind her being at our house most of the time and we didn't have a problem with her being around either. She was a good kid and treated us with nothing but respect.

Sara was an honor roll student, part of the student government, and played on the soccer team with Jenny. She was tall, standing about 5'9" but I didn't notice her other physical traits until later in the spring when the weather got warmer. She wore mostly sweatshirts and sweatpants during the colder months but it was like she was in a cocoon when spring arrived and turned from a caterpillar into a beautiful butterfly. Sara had light brown hair with big brown eyes and a slender, athletic body. She was naturally beautiful and didn't pile on the makeup like a lot of teenagers.

The first time I noticed Sara's physical traits was over dinner one evening. Maryanne and I told the girls to come downstairs to eat and Sara was wearing a sports bra and compression shorts. Apparently, the girls had just finished soccer practice. Sara was in great physical shape with well-defined arm and stomach muscles. Her legs were long, firm and her muscles as equally defined as the rest of her body. Sara had the perfect hourglass figure. The features that struck me about Sara's physique other than her long, slender legs were her full breasts and her ass was round and tight.

I couldn't help but thinking, "Hot damn, how come I never noticed her figure before?"

I had to stop myself from staring. I think Sara noticed my long looks at her, our eyes met and she gave me a simple smile. I felt guilty for looking at her like that, seeing she was my daughter's friend but I was horny from not getting laid and I rationalized it by telling myself that she is eighteen almost nineteen so she was of legal age. I still had to be careful how I looked at her so I wouldn't embarrass my daughter and I didn't want to make Sara feel uncomfortable.

From that day forward, I looked forward to seeing Sara around the house. She knew we didn't mind her being at our house which made her feel more comfortable around my wife and me but that also meant she was there more often. It wasn't unusual for Sara to sleep at our house during the school week which meant I would see her late at night and early in the morning. Jenny liked to sleep in and Maryanne left for the office early so that left me some quiet time in the morning to have a light breakfast and a cup of coffee before getting ready for work.

It became common for Sara to join me for breakfast in the morning whenever she slept over. She was at our house so often, I began to call her my adopted daughter in a light-hearted fashion. I think she enjoyed the attention and the family atmosphere we had in the house. As Sara became more comfortable around our house, she also began to dress more casually around us or should I say around me. When she first started coming around more often, she would be dressed in a sweatshirt and sweatpants in the mornings but as the weather got warmer, Sara began to wear a pair of booty shorts and a tank top to breakfast.

I couldn't help but check out her long legs, tight ass, and full breasts, often reminding myself to stop looking at her like that because she was literally old enough to be my daughter. As she became more comfortable around me, she stopped wearing a bra in the morning when she joined me for breakfast. It was becoming increasingly more difficult to keep my eyes off of her, especially when I could see her brown areola under the haze of her cotton shirt or if her hard nipples were poking out.

Despite my inner guilt feelings, I started to masturbate thinking of Sara and her taut, young body. It seemed the more I tried not to think about her in that way, there more I would picture her when I was alone late at night releasing the pressure in my balls because of the lack of sex with my wife.

Things didn't get easier over time either. Sometimes Sara would join me in the morning wearing an oversized t-shirt that barely covered her tight, firm ass. When she would help make breakfast sometimes I would get a flash of her panties or, if she were wearing a thong, I'd see her bare ass when she was bending over in the refrigerator or getting something from the top cupboard shelf. Seeing her like this was becoming torturous. I enjoyed seeing peeks of Sara's young body but I kept fighting the urge to lust for her also. The conflict in my mind was stressful. It was becoming increasingly more difficult not to think of her when I was jerking off and just gave up fighting not to fantasize about her and all the things I'd like to do with her.

I almost had a heart attack one morning when I was finished getting dressed and Sara came out of the bathroom after taking a shower with just a towel wrapped around her that barely covered her torso. She didn't seem to mind but I was completely distracted. I couldn't help checking her out from her head down to her toes and back again knowing she was stark naked underneath. The devilish side of me was using mental telepathy, hoping her towel would be so loose that it would fall to the floor but I wasn't that fortunate. It's probably a good thing too because I'm not sure I could have controlled myself. I couldn't help but stare at her as she walked to her room. She must have known I was watching her because she turned to look at me over her shoulder and gave me a knowing grin before she went into her room. I began to wonder if she was teasing me on purpose.

On another morning, as I was passing Sara's bedroom on the way to mine to get dressed for work and I noticed her door was cracked open an inch or two. I stopped dead in my tracks and saw that she was completely naked standing in front of her dresser mirror combing her hair. I had dreamed of seeing her nude for months and lady luck gave me an opportunity that morning.

I couldn't help but stare at her luscious, tight, round ass and long legs. I could see her tantalizing, soft, ripe breasts in the reflection of the mirror as well as her neatly trimmed pussy. I swear I almost fainted when she dropped her brush and bent over at the waist to pick it up. I swallowed hard, quelling my desire to rush into her room and make passionate love to her. I could feel a bead of sweat building on my forehead as I watched in silence. I had a brief panic attack when I saw her glance to her left and it appeared that she noticed me watching her.

I thought, "Oh shit, she caught me peeping at her. I hope she doesn't scream or even worse, tell my wife and daughter. What the fuck would I do?"

Instead, Sara got a sly, little grin on her face which told me that if she saw me then she liked me seeing her naked and might have even planned for it to happen. I watched long enough and retreated to my room to get ready for work. I took a few minutes to rub out a quick one before getting dressed. The images of seeing Sara without a stitch of clothing on flashed through my mind for the rest of the day and quite often afterward. To this day, the memory of that morning is forever burned into my brain. Sara never mentioned that day to me and there was no way I was going to say anything.

The more comfortable Sara became around our house, the more I was convinced she was teasing me on purpose. It seemed whenever she was wearing a short skirt, she would happen to have her legs open which gave me a clear upskirt view. For instance, if she were sitting down, she would open her legs, giving me a peek at her panties, as she was getting up while looking directly at me the whole time. It was like Sara was trying to see my reaction. She would then give me that sly grin. In the mornings, she seemed to bend over in front of me more often which gave me a view down her top at her beautifully formed, creamy breasts. After a while, we both knew what was going on with neither one of us acknowledging the little game we were playing.

I wasn't sure if Sara was trying to entice me into making a move on her or if she was simply being a hot, young cock tease looking for confirmation that she could attract the attention of an older man by showing off her body. Either way, there was a line I wasn't going to cross. Nothing good could come from trying to have an affair with my daughter's best friend, in my own house while I was happily married. That didn't stop me from looking at what Sara was showing me and jacking off later. I have to admit, it was tempting and I almost caved into my powerful dick brain a couple of times but I stood strong.

There were times when I would chastise myself for what I was thinking about a teenage friend of my daughter's but then I'd see her again in skin-tight shorts and a crop top and think, "Hot damn, Sara's got a killer body."

As the spring weather turned warmer, it wasn't unusual for Maryanne and me to relax with a drink in our hot tub. We would be joined at times by Jenny and Sara. We'd allow them to have a drink with us in the privacy of our home and under our supervision. I would look forward to those evenings when I wasn't out of town on business because it allowed me to see Sara's flawless, body in a skimpy bikini. You know how a woman you don't find attractive may start looking better after a couple of drinks, well, it's magnified by a thousand times when you've had a few drinks while looking at a beautiful hot, teenager in a barely-there bikini.

I couldn't stare too much with my wife and daughter there but I could still steal a glance at Sara's full breasts that were practically falling out of her top or the cheeks of her ass barely hidden by her bottoms. I always allowed the ladies to leave the hot tub first at the end of the evening, and Sara was almost always directly in front of me. Her bikini would ride up into the crack of her ass and she'd give it a noticeable wiggle climbing the stairs. She wouldn't pull the fabric out from between her cheeks until I got a good look at her ass, then she'd turn around to make sure I was looking. Sara wouldn't be disappointed because I was checking her out every single time.

There were a couple of times when my wife and daughter went to bed early, leaving Sara and me alone in the hot tub. It wouldn't be long before she would say she was too hot (boy, was that an understatement) and sit on the edge to cool off while I was getting hotter in more ways than one. I was free to check out every enticing inch of her dripping wet exposed skin. Her breast hung freely; her long legs looked so good as her painted toes playfully kicked up some churning water. Sara would turn to retrieve her drink while showing me her lovely bikini bottom with her cheeks peeking out from around the edges. It was almost like she was posing for me and I was taking mental pictures for when I'd jerk off later.

We'd have some long conversations which I really enjoyed. She'd tell me things like, "I hope to find a man like you someday, Mr. G (that's what she called me)," or, "You're a good man for letting me live here. I hope I can make it up to you someday."

I didn't know if I should take it as a simple compliment or a come-on. I reassured her that she would eventually find Mr. Right and she didn't have to repay me for anything. I reaffirmed the fact that she was a great person and Maryanne and I were there to give her the support she needed in a difficult time. She took comfort in knowing we thought of her as part of our family. I was happy to be in a financial position to take her under our wing but it also reinforced my guilty feelings for lusting for her.

Sara and I played our little cat and mouse game for the rest of the spring. I knew she was teasing me, and she knew I knew it was intentional. As much as I was tempted, I never acted upon my manly instincts. It was difficult at times, very difficult but I stood firm in more ways than one. Sara seemed to take extra pleasure if she noticed a lump forming in my pants. I continued to jerk off over the images of Sara's body several times per week. I tried to have sex with my wife to help relieve the pressure in my balls but she lost all desire for sex so I was left to take matters into my own hands.

My desires for Sara only increased as the weather got warmer and school was coming to an end. I would see her in her bikini around the pool more often and I got more views of her naked body when she left her bedroom door slightly open for me. The highlight was on prom night. Maryanne took the girls to get their hair and makeup done professionally and got dressed up for their dates.

Jenny wore a simple elegant pink gown that didn't reveal very much of her body except it showed too much cleavage in my opinion but my wife helped her pick it out so I had no say in the matter. Jenny has large breasts and she was putting them on full display. My jaw dropped open when I saw Sara come down the stairs in a silky, form-fitting black gown that hugged every curve of her young, teen body. It had a square front with spaghetti straps and a sultry high cut slit on the left side that showed most of her thigh. She wore ankle strap black high heels. When she walked, the slit would part with the tops of her sheer black stockings and garter now visible. My dick started to stir as I lusted for my daughter's lovely friend once again. They both looked so grown up. I wondered where the time had gone from when Jenny was a little girl playing with dolls to now when she looked like a grown woman.

The girls did a faux runway walk with a turn and my wife asked, "Well, how do they look?"

"You girls are absolutely stunning. I'm afraid to let you leave the house while you're looking so good."

Jenny replied with the familiar, "Oh, dad."

I was half-joking but I knew what would be going through the minds of their horny, teenage dates. That's the problem being a dad. When the boys start coming around the house, we know exactly what they want to do with our daughters. It's our job to cock block them the best we can but, in the end, we all know it's a losing cause.

When I got a good look at Sara's dress from behind, I could see that it perfectly highlighted the curves of her ass. It had a low cut back and it clung tightly to her backside, I wondered if she was wearing underwear. I knew her date was going to try and fuck her that night and it made me a little jealous. I knew I had no right to be envious but she looked so much more mature and absolutely stunning between her sexy dress, hair, makeup, and heels.

As I watched them climb into the limousine with their dates, I couldn't help but wonder not if, but when they would have sex that night. I figured it would probably be at the party they were going to after the prom but I tried as best as I could to not think about it. I should have been more concerned about my daughter but for some reason, I didn't want to think about Sara sucking or fucking anyone. I know it sounds strange but I couldn't help myself.